4 Historic Colonials and Waterfront Escapes in Connecticut and Maine

Originally built in 1910, this tastefully restored Colonial sits in East Rock, directly across from Edgerton Park. A 26-foot entrance foyer with high ceilings sets a gracious tone, anchored by a sweeping staircase and rooms that feel both formal and livable. The living room pairs a fireplace with built-ins, while a paneled library offers a wall of bookcases, its own fireplace, and a hidden bath. Oversize Thermopane replacement windows bring bright, even light throughout. In the formal dining room, leaded-glass built-ins and double French doors open to a spacious sunroom with three exposures, leading out to a private bluestone patio and landscaped, level grounds. The updated, south-facing eat-in kitchen features new appliances and two adjacent pantry spaces, including a second dishwasher and refrigerator. Upstairs, a cozy sitting room overlooks the grounds.

Set along Roosevelt Trail in Naples, “The Naples Barn” blends deep history with contemporary comforts across a thoughtfully reimagined compound. Originally built in 1785, the property now includes three fully renovated Airbnb units—two within the Farmhouse, plus a third created from the Historic Cupola of the Bay of Naples Hotel. Constructed in 1899, the Cupola once overlooked the Naples Causeway until the hotel was demolished in 1960, adding a rare architectural story to the experience. Beyond the accommodations, the barn area operates seasonally as an antique shop, while an end unit serves as a café. Recent upgrades include new windows, a new roof, updated electrical, new septic, improved plumbing, new decks, and fresh asphalt parking. With the Naples Causeway within walking distance, days can easily unfold around restaurants, swimming, boating, fishing, and shopping.

Set on 106 acres of pristine Northern Maine countryside in New Sweden, this restored estate pairs historic heritage with executive-level craftsmanship. A 2009–2011 renovation brought the home down to the studs with new systems—windows, siding, roofing, electrical, heating, septic, and well—plus a poured slab foundation with first-floor radiant heat. A wrap-around porch frames the property’s tranquil privacy, while an attached, heated two-car garage leads into a generous mudroom. The custom kitchen features finely crafted cabinetry, granite countertops, and a professional-grade propane range, alongside a breakfast nook with a propane fireplace and picturesque views. Formal dining, a comfortable living room, and a private office round out the main level. Upstairs, the primary suite offers a soaking tub and tile shower, with two additional bedrooms, a shared bath, and a laundry center. Above the garage, a finished suite adds flexibility, and an extensively restored barn and functioning windmill complete the setting.

Along the water’s edge in Skowhegan, this beautifully updated post-and-beam ranch balances privacy with room to breathe and miles of water for fishing, boating, canoeing, kayaking, paddleboarding, and swimming. Inside, spacious rooms unfold in an open-concept layout, where cascading natural light moves easily throughout the home. The kitchen is tailored for everyday cooking and effortless hosting, with granite countertops, updated appliances including an induction oven, and a convenient island that keeps conversation close at hand. Living and dining areas are finished with hardwood floors, cathedral ceilings, and exposed beams, creating a warm sense of volume without losing intimacy. Throughout, the setting stays present, with views over the grounds that keep daily life connected to the outdoors. Days here can begin on the water and end beneath those soaring ceilings.